A friend of mine has been deep into exploring a big job change, and in the process really thinking about how it fits into a long-term career plan. This isn't a career change situation, mind you, but more of a job change that aligns with advancing goals. I've seen people do it countless times, but never thought much about what the motivation is.
I usually associate these kinds of things with very Type-A people who have no work-life balance, but my friend is mostly not that kind of person. Having a career path in mind is probably a good idea no matter what your personality tendencies are, because it helps guide your potential into something tangible.
I'm very classically Type-B, though I definitely borrow from the other category in some ways (primarily the desire for people to communicate efficiently). This implies that I'm very go-with-the-flow, and in terms of career, I think that maybe I have been to some degree. There were a couple of years, from 2002 to 2006, where I wasn't thinking about career in any serious way at all, and drifted from one thing to another in a non-deliberate fashion. Some good things came out of that, not the least of which was my book and an intense season of coaching high school volleyball.
When I was in college, I had it all figured out. I was going to be a superstar DJ and own a radio station. It took me less than a year to realize how awful that business was, and then I spent three years doing (and enjoying) local government cable TV. When the Internet came calling, that was the start of the transition to software development (1999), and I've been at it ever since.
But I never had a plan, a long-term goal, or any real sense of what I wanted to be when I grew up. And really, why would I? Not counting the crappy on and off employment years (2004, 2008, 2009), I was still managing to double my income every few years. I always thought about what I would enjoy doing, but never thought of it much in the context of job titles or scope of responsibility.
Then I ended up at Microsoft. As much as I have certain issues with their angle on career development, I still ended up having to think a lot about what I wanted to do. It was clear at that point that I did not want to be a heads-down code monkey, and going down the path toward technical fellow (like the dudes who write entire languages) was not something I felt capable of. I did, however, enjoy more of the technical design work, managing people, prototyping stuff and improving process. These were all things I was very good at in the short-term consulting gigs I had. Finding something at Microsoft that allowed me to do that variety of things was shockingly hard, in part because of a recurring theme of "how we do it at Microsoft." There was one gig I interviewed for in the Xbox org that was all of these things, but while I "passed" the interview loop, the other guy who applied was just slightly more experienced than me, so they gave it to him.
At Humana I got to use a lot of these skills in a role that wasn't technically the domain of software architecture, but because that company lacked a lot of experience (and had its own bubble problems), it's largely what I got to do. It was the first time in my post-broadcast life that I understood what I was really good at, and what the job looked like.
Once we were ready to move on from Cleveland, finally able to sell the house, I happened to align with just the right thing at SeaWorld Parks, and I'm getting to do similar work to the Humana job, only this time it's in a better environment, and my inner-carnie loves the subject matter.
The work in the last year and a half has really made me think about a long-term goal. Technical leadership is clearly where I want to be. The question then becomes, what does that look like? Is it a CTO/CIO kind of job at a company of similar size? Is it me running my own company? The size of the company really dictates whether or not I would be qualified to do the job today. If I had to put a number on it, probably not with an org larger than 40 to 50. I would like to think, perhaps naively, that coming up through the technical ranks while being able to do the work (most upper management tends to be straight management career types) is an advantage.
Still, given my Type-B personality, I'm totally open to a different path, and would probably be content to run some little company that did a few 100k in revenue a year publishing cat photos on the Intertubes. Not going all-in toward some goal doesn't make you weak or a slacker, it just means you're open to constant revision based on your continuing acquisition of experience.